Adrenochrome isonicotinic acid hydrazone



United States Patent ADRENGCHROME ISONIQOTINEC ACID HYDRAZONE NoDrawing. Application December 9, 1953, Serial No. 397,273

1 Claim. (Cl. 260-295) The present invention relates to a noveladrenochrome derivative.

More particularly, the present invention relates to the novel compoundadrenochrome isonicotinic acid hydrazone and to a process for theproduction thereof.

In the United States Patent Number 2,506,294, of May 2, 1950, there isdisclosed certain adrenochrome derivatives such as the mono-oxime,semicarbazone, etc. in accordance with the patent, these adrenochromederivatives are produced by reacting salts of hydroxylamine orsemicarbazide with adrenochrome. The resultant products are stated to bestable derivatives of adrenochrome having valuable haemostaticproperties.

In accordance with the present invention, it has been discovered thatstill another adrenochrome derivative having valuable haemostaticproperties may be prepared by the reaction of isonicotinic acidhydrazide with adrenochrome. The resultant compound, the isonicotinicacid hydrazone of adrenochrome is a valuable .haemostat and especiallywhen used, in the form of a complex or other combination, with non-toxicwater soluble salts such as the sodium salt of 3-hydroxy-2-naphthoicacid as more fully described in the copending application ofFleischhacker and Barsel, Serial Number 397,268, filed as of even dateherewith.

The following reaction serves to illustrate the process of the presentinvention.

In proceeding in accordance with the above equation, a suitable quantityof adrenochrome is dissolved in an ethyl alcohol-water solution(containing 80% by volume Cir 2,728,772 Eatented Dec. 27, 1955 of ethylalcohol) so as to form a clear solution, approximately 20 cc. of solventbeing utilized for each gram of adrenochrome. Thereafter, a solution ofisonicotinic acid hydrazide dissolved in alcohol is added thereto. Thereaction solution is then allowed to stand at room temperature overnight. The resultant precipitate of isonicotinic acid hydrazone ofadrenochrome is then filtered from the reaction mixture and washed Withethyl alcohol.

Although it is preferred to form the hydrazone by reaction in an ethylalcohol-Water solution as hereinbefore described, other solutions oflower aliphatic alcohols may be used or other compatible inert organicsolvents. Fuither, although the reaction at approximately roomtemperature is preferable, careful heating may be employed for shorterperiods.

The following specific example serves to illustrate but is not intendedto limit the present invention:

Example 210-213 C., with decomposition and the following formula:

o:NH-N OH I \N \N OH:

I claim:

The isonicotinic acid hydrazone of adrenochrome hav ing the followingformula:

N \N (1H1 References Cited in the file of this patent UNITED STATESPATENTS 2,506,294 Dechamps May 2, 1950 2,581,850 Fleischhacker Jan. 8,1952 2,655,510 Sobotka Oct. 13, 1953 OTHER REFERENCES Sidgwick: Org.Chem. of Nitrogen, page 393 (1937).

